Marine Drugs

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23 pages, 6282 KiB

Open AccessArticle

Anthraquinone Derivatives and Other Aromatic Compounds from Marine Fungus Asteromyces cruciatus KMM 4696 and Their Effects against Staphylococcus aureus

by Olesya I. Zhuravleva, Ekaterina A. Chingizova, Galina K. Oleinikova, Sofya S. Starnovskaya, Alexandr S. Antonov, Natalia N. Kirichuk, Alexander S. Menshov, Roman S. Popov, Natalya Yu. Kim, Dmitrii V. Berdyshev, Artur R. Chingizov, Alexandra S. Kuzmich, Irina V. Guzhova, Anton N. Yurchenko and Ekaterina A. Yurchenko

Mar. Drugs 2023, 21(8), 431; https://0-doi-org.brum.beds.ac.uk/10.3390/md21080431 - 29 Jul 2023

Cited by 1 | Viewed by 1365

Abstract

New anthraquinone derivatives acruciquinones A–C (1–3), together with ten known metabolites, were isolated from the obligate marine fungus Asteromyces cruciatus KMM 4696. Acruciquinone C is the first member of anthraquinone derivatives with a 6/6/5 backbone. The structures of isolated [...] Read more.

New anthraquinone derivatives acruciquinones A–C (1–3), together with ten known metabolites, were isolated from the obligate marine fungus Asteromyces cruciatus KMM 4696. Acruciquinone C is the first member of anthraquinone derivatives with a 6/6/5 backbone. The structures of isolated compounds were established based on NMR and MS data. The absolute stereoconfigurations of new acruciquinones A–C were determined using ECD and quantum chemical calculations (TDDFT approach). A plausible biosynthetic pathway of the novel acruciquinone C was proposed. Compounds 1–4 and 6–13 showed a significant antimicrobial effects against Staphylococcus aureus growth, and acruciquinone A (1), dendryol B (4), coniothyrinone B (7), and ω-hydroxypachybasin (9) reduced the activity of a key staphylococcal enzyme, sortase A. Moreover, the compounds, excluding 4, inhibited urease activity. We studied the effects of anthraquinones 1, 4, 7, and 9 and coniothyrinone D (6) in an in vitro model of skin infection when HaCaT keratinocytes were cocultivated with S. aureus. Anthraquinones significantly reduce the negative impact of S. aureus on the viability, migration, and proliferation of infected HaCaT keratinocytes, and acruciquinone A (1) revealed the most pronounced effect. Full article

(This article belongs to the Special Issue Bioactive Secondary Metabolites of Marine Fungi)

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10 pages, 2044 KiB

Open AccessArticle

Diketopiperazine Alkaloids and Bisabolene Sesquiterpenoids from Aspergillus versicolor AS-212, an Endozoic Fungus Associated with Deep-Sea Coral of Magellan Seamounts

by Yu-Liang Dong, Xiao-Ming Li, Xiao-Shan Shi, Yi-Ran Wang, Bin-Gui Wang and Ling-Hong Meng

Mar. Drugs 2023, 21(5), 293; https://0-doi-org.brum.beds.ac.uk/10.3390/md21050293 - 10 May 2023

Cited by 1 | Viewed by 1381

Abstract

Two new quinazolinone diketopiperazine alkaloids, including versicomide E (2) and cottoquinazoline H (4), together with ten known compounds (1, 3, and 5–12) were isolated and identified from Aspergillus versicolor AS-212, an endozoic fungus [...] Read more.

Two new quinazolinone diketopiperazine alkaloids, including versicomide E (2) and cottoquinazoline H (4), together with ten known compounds (1, 3, and 5–12) were isolated and identified from Aspergillus versicolor AS-212, an endozoic fungus associated with the deep-sea coral Hemicorallium cf. imperiale, which was collected from the Magellan Seamounts. Their chemical structures were determined by an extensive interpretation of the spectroscopic and X-ray crystallographic data as well as specific rotation calculation, ECD calculation, and comparison of their ECD spectra. The absolute configurations of (−)-isoversicomide A (1) and cottoquinazoline A (3) were not assigned in the literature reports and were solved in the present work by single-crystal X-ray diffraction analysis. In the antibacterial assays, compound 3 exhibited antibacterial activity against aquatic pathogenic bacteria Aeromonas hydrophilia with an MIC value of 18.6 μM, while compounds 4 and 8 exhibited inhibitory effects against Vibrio harveyi and V. parahaemolyticus with MIC values ranging from 9.0 to 18.1 μM. Full article

(This article belongs to the Special Issue Bioactive Secondary Metabolites of Marine Fungi)

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11 pages, 2738 KiB

Open AccessArticle

Thiolactones and Δ^8,9-Pregnene Steroids from the Marine-Derived Fungus Meira sp. 1210CH-42 and Their α-Glucosidase Inhibitory Activity

by Hee Jae Shin, Min Ah Lee, Hwa-Sun Lee and Chang-Su Heo

Mar. Drugs 2023, 21(4), 246; https://0-doi-org.brum.beds.ac.uk/10.3390/md21040246 - 16 Apr 2023

Cited by 1 | Viewed by 1338

Abstract

The fungal genus Meira was first reported in 2003 and has mostly been found on land. This is the first report of second metabolites from the marine-derived yeast-like fungus Meira sp. One new thiolactone (1), along with one revised thiolactone ( [...] Read more.

The fungal genus Meira was first reported in 2003 and has mostly been found on land. This is the first report of second metabolites from the marine-derived yeast-like fungus Meira sp. One new thiolactone (1), along with one revised thiolactone (2), two new Δ^8,9-steroids (4, 5), and one known Δ^8,9-steroid (3), were isolated from the Meira sp. 1210CH-42. Their structures were elucidated based on the comprehensive spectroscopic data analysis of 1D, 2D NMR, HR-ESIMS, ECD calculations, and the pyridine-induced deshielding effect. The structure of 5 was confirmed by oxidation of 4 to semisynthetic 5. In the α-glucosidase inhibition assay, compounds 2–4 showed potent in vitro inhibitory activity with IC₅₀ values of 148.4, 279.7, and 86.0 μM, respectively. Compounds 2–4 exhibited superior activity as compared to acarbose (IC₅₀ = 418.9 μM). Full article

(This article belongs to the Special Issue Bioactive Secondary Metabolites of Marine Fungi)

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16 pages, 4087 KiB

Open AccessArticle

Noonindoles A–F: Rare Indole Diterpene Amino Acid Conjugates from a Marine-Derived Fungus, Aspergillus noonimiae CMB-M0339

by Sarani Kankanamge, Zeinab G. Khalil, Paul V. Bernhardt and Robert J. Capon

Mar. Drugs 2022, 20(11), 698; https://0-doi-org.brum.beds.ac.uk/10.3390/md20110698 - 07 Nov 2022

Cited by 3 | Viewed by 2198

Abstract

Analytical scale chemical/cultivation profiling prioritized the Australian marine-derived fungus Aspergillus noonimiae CMB-M0339. Subsequent investigation permitted isolation of noonindoles A–F (5–10) and detection of eight minor analogues (i–viii) as new examples of a rare class of [...] Read more.

Analytical scale chemical/cultivation profiling prioritized the Australian marine-derived fungus Aspergillus noonimiae CMB-M0339. Subsequent investigation permitted isolation of noonindoles A–F (5–10) and detection of eight minor analogues (i–viii) as new examples of a rare class of indole diterpene (IDT) amino acid conjugate, indicative of an acyl amino acid transferase capable of incorporating a diverse range of amino acid residues. Structures for 5–10 were assigned by detailed spectroscopic and X-ray crystallographic analysis. The metabolites 5–14 exhibited no antibacterial properties against G-ve and G+ve bacteria or the fungus Candida albicans, with the exception of 5 which exhibited moderate antifungal activity. Full article

(This article belongs to the Special Issue Bioactive Secondary Metabolites of Marine Fungi)

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19 pages, 1862 KiB

Open AccessArticle

New Alkylpyridinium Anthraquinone, Isocoumarin, C-Glucosyl Resorcinol Derivative and Prenylated Pyranoxanthones from the Culture of a Marine Sponge-Associated Fungus, Aspergillus stellatus KUFA 2017

by Fátima P. Machado, Inês C. Rodrigues, Luís Gales, José A. Pereira, Paulo M. Costa, Tida Dethoup, Sharad Mistry, Artur M. S. Silva, Vitor Vasconcelos and Anake Kijjoa

Mar. Drugs 2022, 20(11), 672; https://0-doi-org.brum.beds.ac.uk/10.3390/md20110672 - 27 Oct 2022

Cited by 3 | Viewed by 3048

Abstract

An unreported isocoumarin, (3S,4R)-4-hydroxy-6-methoxymellein (2), an undescribed propylpyridinium anthraquinone (4), and an unreported C-glucosyl resorcinol derivative, acetyl carnemycin E (5c), were isolated, together with eight previously reported metabolites including p-hydroxybenzaldehyde (1 [...] Read more.

An unreported isocoumarin, (3S,4R)-4-hydroxy-6-methoxymellein (2), an undescribed propylpyridinium anthraquinone (4), and an unreported C-glucosyl resorcinol derivative, acetyl carnemycin E (5c), were isolated, together with eight previously reported metabolites including p-hydroxybenzaldehyde (1), 1,3-dimethoxy-8-hydroxy-6-methylanthraquinone (3a), 1,3-dimethoxy-2,8-dihydroxy-6-methylanthraquinone (3b), emodin (3c), 5[(3E,5E)-nona-3,5-dien-1-yl]benzene (5a), carnemycin E (5b), tajixanthone hydrate (6a) and 15-acetyl tajixanthone hydrate (6b), from the ethyl acetate extract of the culture of a marine sponge-derived fungus, Aspergillus stellatus KUFA 2017. The structures of the undescribed compounds were elucidated by 1D and 2D NMR and high resolution mass spectral analyses. In the case of 2, the absolute configurations of the stereogenic carbons were determined by comparison of their calculated and experimental electronic circular dichroism (ECD) spectra. The absolute configurations of the stereogenic carbons in 6a and 6b were also determined, for the first time, by X-ray crystallographic analysis. Compounds 2, 3a, 3b, 4, 5a, 5b, 5c, 6a, and 6b were assayed for antibacterial activity against four reference strains, viz. two Gram-positive (Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212) and two Gram-negative (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853), as well as three multidrug-resistant strains. However, only 5a exhibited significant antibacterial activity against both reference and multidrug-resistant strains. Compound 5a also showed antibiofilm activity against both reference strains of Gram-positive bacteria. Full article

(This article belongs to the Special Issue Bioactive Secondary Metabolites of Marine Fungi)

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10 pages, 2137 KiB

Open AccessArticle

Anti-inflammatory Polyketides from the Marine-Derived Fungus Eutypella scoparia

by Ya-Hui Zhang, Hui-Fang Du, Wen-Bin Gao, Wan Li, Fei Cao and Chang-Yun Wang

Mar. Drugs 2022, 20(8), 486; https://0-doi-org.brum.beds.ac.uk/10.3390/md20080486 - 28 Jul 2022

Cited by 6 | Viewed by 1825

Abstract

Three new polyketides, eutyketides A and B (1 and 2) and cytosporin X (3), along with four known compounds (4–7), were obtained from the marine-derived fungus Eutypella scoparia. The planar structures of 1 and [...] Read more.

Three new polyketides, eutyketides A and B (1 and 2) and cytosporin X (3), along with four known compounds (4–7), were obtained from the marine-derived fungus Eutypella scoparia. The planar structures of 1 and 2 were elucidated by extensive HRMS and 1D and 2D NMR analyses. Their relative configurations of C-13 and C-14 were determined with chemical conversions by introducing an acetonylidene group. The absolute configurations of 1–3 were determined by comparing their experimental electronic circular dichroism (ECD) data with their computed ECD results. All of the isolated compounds were tested for their anti-inflammatory activities on lipopolysaccharide-induced nitric oxide production in RAW 264.7 macrophages. Compounds 5 and 6 showed stronger anti-inflammatory activities than the other compounds, with the inhibition of 49.0% and 54.9% at a concentration of 50.0 µg/mL, respectively. Full article

(This article belongs to the Special Issue Bioactive Secondary Metabolites of Marine Fungi)

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11 pages, 1754 KiB

Open AccessArticle

Exophilone, a Tetrahydrocarbazol-1-one Analogue with Anti-Pulmonary Fibrosis Activity from the Deep-Sea Fungus Exophiala oligosperma MCCC 3A01264

by Ming-Jun Hong, Meng-Jiao Hao, Guang-Yu Zhang, Hou-Jin Li, Zong-Ze Shao, Xiu-Pian Liu, Wen-Zhe Ma, Jun Xu, Taifo Mahmud and Wen-Jian Lan

Mar. Drugs 2022, 20(7), 448; https://0-doi-org.brum.beds.ac.uk/10.3390/md20070448 - 09 Jul 2022

Cited by 3 | Viewed by 2052

Abstract

A new compound, exophilone (1), together with nine known compounds (2–10), were isolated from a deep-sea-derived fungus, Exophiala oligosperma. Their chemical structures, including the absolute configuration of 1, were elucidated using nuclear magnetic resonance (NMR) spectroscopy, [...] Read more.

A new compound, exophilone (1), together with nine known compounds (2–10), were isolated from a deep-sea-derived fungus, Exophiala oligosperma. Their chemical structures, including the absolute configuration of 1, were elucidated using nuclear magnetic resonance (NMR) spectroscopy, high-resolution electrospray ionization mass spectroscopy (HRESIMS), and electronic circular dichroism (ECD) calculation. Compounds were preliminarily screened for their ability to inhibit collagen accumulation. Compounds 1, 4, and 7 showed weaker inhibition of TGF-β1-induced total collagen accumulation in compared with pirfenidone (73.14% inhibition rate). However, pirfenidone exhibited cytotoxicity (77.57% survival rate), while compounds 1, 4, and 7 showed low cytotoxicity against the HFL1 cell line. Particularly, exophilone (1) showed moderate collagen deposition inhibition effect (60.44% inhibition rate) and low toxicity in HFL1 cells (98.14% survival rate) at a concentration of 10 μM. A molecular docking study suggests that exophilone (1) binds to both TGF-β1 and its receptor through hydrogen bonding interactions. Thus, exophilone (1) was identified as a promising anti-pulmonary fibrosis agent. It has the potential to be developed as a drug candidate for pulmonary fibrosis. Full article

(This article belongs to the Special Issue Bioactive Secondary Metabolites of Marine Fungi)

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18 pages, 2945 KiB

Open AccessArticle

Discovery of Anti-MRSA Secondary Metabolites from a Marine-Derived Fungus Aspergillus fumigatus

by Rui Zhang, Haifeng Wang, Baosong Chen, Huanqin Dai, Jingzu Sun, Junjie Han and Hongwei Liu

Mar. Drugs 2022, 20(5), 302; https://0-doi-org.brum.beds.ac.uk/10.3390/md20050302 - 28 Apr 2022

Cited by 9 | Viewed by 3047

Abstract

Methicillin-resistant Staphylococcus aureus (MRSA), a WHO high-priority pathogen that can cause great harm to living beings, is a primary cause of death from antibiotic-resistant infections. In the present study, six new compounds, including fumindoline A–C (1–3), 12β, [...] Read more.

Methicillin-resistant Staphylococcus aureus (MRSA), a WHO high-priority pathogen that can cause great harm to living beings, is a primary cause of death from antibiotic-resistant infections. In the present study, six new compounds, including fumindoline A–C (1–3), 12β, 13β-hydroxy-asperfumigatin (4), 2-epi-tryptoquivaline F (17) and penibenzophenone E (37), and thirty-nine known ones were isolated from the marine-derived fungus Aspergillus fumigatus H22. The structures and the absolute configurations of the new compounds were unambiguously assigned by spectroscopic data, mass spectrometry (MS), electronic circular dichroism (ECD) spectroscopic analyses, quantum NMR and ECD calculations, and chemical derivatizations. Bioactivity screening indicated that nearly half of the compounds exhibit antibacterial activity, especially compounds 8 and 11, and 33–38 showed excellent antimicrobial activities against MRSA, with minimum inhibitory concentration (MIC) values ranging from 1.25 to 2.5 μM. In addition, compound 8 showed moderate inhibitory activity against Mycobacterium bovis (MIC: 25 μM), compound 10 showed moderate inhibitory activity against Candida albicans (MIC: 50 μM), and compound 13 showed strong inhibitory activity against the hatching of a Caenorhabditis elegans egg (IC₅₀: 2.5 μM). Full article

(This article belongs to the Special Issue Bioactive Secondary Metabolites of Marine Fungi)

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Review

Jump to: Research

53 pages, 4206 KiB

Open AccessReview

Secondary Metabolites, Biological Activities, and Industrial and Biotechnological Importance of Aspergillus sydowii

by Sabrin R. M. Ibrahim, Shaimaa G. A. Mohamed, Baiaan H. Alsaadi, Maryam M. Althubyani, Zainab I. Awari, Hazem G. A. Hussein, Abrar A. Aljohani, Jumanah Faisal Albasri, Salha Atiah Faraj and Gamal A. Mohamed

Mar. Drugs 2023, 21(8), 441; https://0-doi-org.brum.beds.ac.uk/10.3390/md21080441 - 05 Aug 2023

Cited by 6 | Viewed by 1904

Abstract

Marine-derived fungi are renowned as a source of astonishingly significant and synthetically appealing metabolites that are proven as new lead chemicals for chemical, pharmaceutical, and agricultural fields. Aspergillus sydowii is a saprotrophic, ubiquitous, and halophilic fungus that is commonly found in different marine [...] Read more.

Marine-derived fungi are renowned as a source of astonishingly significant and synthetically appealing metabolites that are proven as new lead chemicals for chemical, pharmaceutical, and agricultural fields. Aspergillus sydowii is a saprotrophic, ubiquitous, and halophilic fungus that is commonly found in different marine ecosystems. This fungus can cause aspergillosis in sea fan corals leading to sea fan mortality with subsequent changes in coral community structure. Interestingly, A. sydowi is a prolific source of distinct and structurally varied metabolites such as alkaloids, xanthones, terpenes, anthraquinones, sterols, diphenyl ethers, pyrones, cyclopentenones, and polyketides with a range of bioactivities. A. sydowii has capacity to produce various enzymes with marked industrial and biotechnological potential, including α-amylases, lipases, xylanases, cellulases, keratinases, and tannases. Also, this fungus has the capacity for bioremediation as well as the biocatalysis of various chemical reactions. The current work aimed at focusing on the bright side of this fungus. In this review, published studies on isolated metabolites from A. sydowii, including their structures, biological functions, and biosynthesis, as well as the biotechnological and industrial significance of this fungus, were highlighted. More than 245 compounds were described in the current review with 134 references published within the period from 1975 to June 2023. Full article

(This article belongs to the Special Issue Bioactive Secondary Metabolites of Marine Fungi)

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19 pages, 4983 KiB

Open AccessReview

Natural Products from Chilean and Antarctic Marine Fungi and Their Biomedical Relevance

by Dioni Arrieche, Jaime R. Cabrera-Pardo, Aurelio San-Martin, Héctor Carrasco and Lautaro Taborga

Mar. Drugs 2023, 21(2), 98; https://0-doi-org.brum.beds.ac.uk/10.3390/md21020098 - 29 Jan 2023

Cited by 4 | Viewed by 2024

Abstract

Fungi are a prolific source of bioactive molecules. During the past few decades, many bioactive natural products have been isolated from marine fungi. Chile is a country with 6435 Km of coastline along the Pacific Ocean and houses a unique fungal biodiversity. This [...] Read more.

Fungi are a prolific source of bioactive molecules. During the past few decades, many bioactive natural products have been isolated from marine fungi. Chile is a country with 6435 Km of coastline along the Pacific Ocean and houses a unique fungal biodiversity. This review summarizes the field of fungal natural products isolated from Antarctic and Chilean marine environments and their biological activities. Full article

(This article belongs to the Special Issue Bioactive Secondary Metabolites of Marine Fungi)

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